反应 #554676

反应方程式

tert-Butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate

sodium carbonate

→

sub-title product

收率 89.0%

tert-Butyl N-tert-butoxycarbonyl-N-[3-ethynyl-5-(4-isopropylsulfonylphenyl)pyrazin-2-yl]carbamate

收率 89.0%

溶剂

methanol

反应条件

后处理

1. 1
   其他An oil separated out
2. 2
   workup.ADDITIONmore methanol (100 mL) was added
3. 3
   workup.DISSOLUTIONto dissolve
4. 4
   workup.ADDITIONThe slurry was poured into a mixture of EtOAc/water (800 mL/1 L)
5. 5
   其他The organic phase was separated
6. 6
   萃取the aqueous extracted with EtOAc (2×250 mL)
7. 7
   洗涤The combined organic extracts were washed with brine
8. 8
   干燥dried (MgSO4)
9. 9
   过滤filtered
10. 10
    浓缩concentrated in vacuo
11. 11
    workup.STIRRINGstirred for 90 minutes at ambient temperature
12. 12
    其他The precipitate was isolated by filtration
13. 13
    洗涤washed with Petroleum Ether
14. 14
    其他dried

实验过程

tert-Butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate (42.6 g, 74.25 mmol) was dissolved/suspended in methanol (510 mL) and 2M aqueous sodium carbonate (425.8 mL, 851.6 mmol) was added to the rapidly stirred mixture. An oil separated out and more methanol (100 mL) was added to dissolve. The mixture was stirred at ambient temperature for 1 hour. The slurry was poured into a mixture of EtOAc/water (800 mL/1 L). The organic phase was separated and the aqueous extracted with EtOAc (2×250 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was slurried in 5% EtOAc/Petroleum Ether and stirred for 90 minutes at ambient temperature. The precipitate was isolated by filtration, washed with Petroleum Ether and dried to give the sub-title product as a white solid (33.1 g, 89% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.18 (d, 6H), 1.37 (s, 18H), 3.50 (sept, 1H), 4.99 (s, 1H), 8.03 (d, 2H), 8.44 (d, 2H) and 9.35 (s, 1H) ppm; MS (ES+) 502.1.

来源